There are two schools of thought on Hugh Hefner. According to one school, he’s a skeevy old has-been in his pajamas who created this cheesy media company in the dark ages that exploited both bunnies and women, and who now stars in a D-grade reality show. According to the other school he’s the coolest guy who ever lived. Both schools got a shock on the day after Christmas when the 84-year-old’s Twitter stream announced that he was engaged.

His intended bride is Crystal Harris, a 24 year old British-American citizen. She has been in Hef’s harem on E!’s The Girls Next Door, along with the Shannon twins, since 2009. Despite her youth, this is sort of a December-December romance—she was Playboy‘s Miss December last year. No mere plaything, she also has one of those hard-to-snag recording contracts and plans to launch a cosmetics line. (More on Time.com:Has Infidelity Gone Legit? It Nabs a Starring Role in The New York Times)

We wish the couple all the very best and a long and richly fulfilling married life. But nagging questions remain, like: why? Speaking from a pure business perspective, Harris gets quite a lot in this deal: run of the mansion, access to Playboy Enterprises media properties, a lot of exposure, high-end lifestyle, as much bunny-themed merchandise as any girl could reasonably wish for, plus a slice of the estate, when the time comes.

What does Hef get? We’re guessing he has good lawyers, so that he, or his children, won’t lose too much if it all goes belly-up. But what does marrying Harris bring him that having her on his reality show didn’t? In both cases she’s more or less contractually obliged to keep him company, tend to his needs and sleep in his bed. (Co-starring in a reality show is so similar to being legally wed, in fact, that somebody might want to look into it as a way forward in the gay marriage debate. ) (More on Time.com:Why Married Men Are Less Antisocial)

So why buy Harris the ring? Could it be that Hef is actually a romantic and wants his No. 1 girlfriend to have it all? He only recently divorced his second wife, although they had been separated for some years. He gave his daughter Christie control over the Playboy business several years ago. If you ignore the whole bit about how pornography objectifies and dehumanizes women and messes with the sexual lives of men, often leading to addiction and an inability to have healthy relationships with their girlfriends and wives, he doesn’t seem all that un-gallant.

But something less sentimental might also be afoot in the Playboy playpen. Hef’s last No. 1 girlfriend, Holly Madison, reportedly left his home and the show out of frustration with not being able to build a marriage or have a family with him. The Shannon twins also recently departed the Playboy Mansion, although they’re still on the show. The show’s ratings and the financial health of the Playboy enterprise are in decline. And reality show contracts have no for-richer-or-poorer-clause. (More on Time.com: How Prince William is the Model Modern Groom)

Since it’s not likely Hef would suddenly discover his warm, fuzzy and marriage-friendly side now, in the ninth decade of life, maybe he’s is feeling the shadow of the aging Lothario’s biggest bogeyman: being alone. Let’s hope he knows marriage is no guarantee against that.

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